Isocyano dihydropyridones accessible via a recently reported multicomponent reaction react with aldehydes and amines to afford dihydrooxazolopyridines in high yield. The scope and limitations of this novel multicomponent reaction were investigated. The efficient combination of two highly variable multicomponent reactions allows the construction of a very broad range of dihydrooxazolopyridines, an unexplored class of bicyclic compounds. The implications of the observed reactivity profile for the mechanism of this multicomponent reaction are discussed.
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http://dx.doi.org/10.1021/ol802515v | DOI Listing |
Org Biomol Chem
January 2025
Jiangxi Provincial Key Laboratory of Functional Crystalline Materials Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, Jiangxi Province, P.R. China.
The multi-component ring-opening reactions of cyclic ethers offer an efficient strategy for the rapid introduction of multiple functional groups and the construction of complex molecular architectures. Despite the minimal ring strain in five- and six-membered rings presenting a significant challenge for ring-opening, advancements have been made. Traditional acid-catalyzed pathways have been complemented by a novel approach involving carbene-induced oxonium intermediate formation, which has emerged in recent years and expanded the selectivity of ring-opening reactions.
View Article and Find Full Text PDFLangmuir
January 2025
Department of Chemical Engineering and Materials Research Institute, Pennsylvania State University, University Park, Pennsylvania 16802, United States.
The chemical reactivity of glass surfaces is often studied with elemental analysis techniques, and although such characterization methods provide insights on compositional changes from exposure to specific chemical conditions, molecule-specific chemical reactions are not determined unambiguously. This study demonstrates the use of reflection-absorption infrared spectroscopy (RAIRS) to detect molecular species on alkali-free boroaluminosilicate and alkali aluminosilicate glasses, using acetic acid vapor as a model reactant to probe reaction sites at the surface with or without pretreatment by aqueous solutions of varied pH. With the assistance of the theoretical calculation of spectral changes based on refractive indices of bulk materials, it was possible to identify the molecular species being removed and produced at the glass surface.
View Article and Find Full Text PDFChemistry
January 2025
Shandong University, Chemistry, shandananlv 27hao, 250100, Jinan, CHINA.
A straightforward I2-promoted Povarov multicomponent reaction strategy for the synthesis of N-heteroaromatic benzothiazole and 2, 2'-biquinolines was described. This methodology involved a one-pot two-step procedure, tandem iodination/Kornblum oxidation, and [4 + 2] condensation. This protocol was characterized by broad scope of substrates (49 examples, 31-80% yields), applicable for large-scale preparation, and downstream derivatization of the product.
View Article and Find Full Text PDFChemMedChem
January 2025
Central University of Haryana, Chemistry, Academic Block-1, Jant-Pali, 123 031, Mahendergarh, INDIA.
Multicomponent reactions have long been recognized as some of the most versatile tools in organic chemistry, with extensive applications in biomedical science and the pharmaceutical industry. In this study, we explored the potential of the Passerini reaction by designing and synthesizing new low molecular mass gelators that can serve as novel formulations for prolonged anesthesia. These gelators address critical issues like poor solubility, low bioavailability, and short plasma half-life, all of which hinder therapeutic efficacy.
View Article and Find Full Text PDFBeilstein J Org Chem
January 2025
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 9, 22100, Como, Italy.
This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic insights were outlined as well as cycloaddition and aza-Diels-Alder reactions were included. These strategies have gained attention due to their highly atom- and step-economy, one-step multi-bond forming, mild reaction conditions, low cost and easy handling.
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